Purpose: The purpose of this paper is to look across six first-year principals to investigate their engagement with and sensemaking of specific messages of instructional leadership around teacher evaluation. Design/methodology/approach: This research project, a cross-case study, was carried out using in-depth qualitative observations and interviews of six first-year principals over one school year. Sensemaking theory was used to analyze both how and the mechanisms through which principals understood their roles as teacher evaluators. Findings: The results demonstrate that first, principals received a variety of messages about how to conduct teacher evaluations, and second, that connections to specific individuals influenced their associations to specific messages they received about instructional leadership and how they enacted teacher evaluation practices on their campuses. Research limitations/implications: This is an in-depth qualitative analysis, and therefore is not generalizable to all first-year principals, school districts, or principal preparation programs. However, it adds to the field's understanding of the meso level of policy implementation, highlighting the process of individuals' sensemaking and the importance of their informal connections in the associations they make to messages about instructional leadership. Practical implications: This research adds to the field of principal preparation and induction as it highlights what is important for first-year principals as they build their professional identities. Further, it highlights the variability in principals' understanding and enactment of teacher evaluation policies, an important feature as this practice is coming to the fore both in current practice and research. Originality/value: This study adds to an understanding of institutional theory by looking at the interaction between the organizational levels, and further explicates individual actors' agency within a socio-organizational context. The findings also add to a dearth of empirical studies on the routine of teacher evaluation from the principal perspective.